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Identification
NamePorphobilinogen
Accession NumberDB02272  (EXPT02507)
TypeSmall Molecule
GroupsExperimental
DescriptionPorphobilinogen is a pyrrole involved in porphyrin metabolism. It is generated by the enzyme ALA dehydratase, and converted into hydroxymethyl bilane by the enzyme porphobilinogen deaminase.
Structure
Thumb
Synonyms
2-aminomethylpyrrol-3-acetic acid 4-propionic acid
5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propionic acid
PBG
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII74KHC72QXK
CAS number487-90-1
WeightAverage: 225.2212
Monoisotopic: 225.087531914
Chemical FormulaC10H13N2O4
InChI KeyInChIKey=YPHQRHBJEUDWJW-UHFFFAOYSA-N
InChI
InChI=1S/C10H13N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5H,1-4,11H2,(H,13,14)(H,15,16)
IUPAC Name
3-[5-(aminomethyl)-4-(carboxymethyl)pyrrol-3-yl]propanoic acid
SMILES
NCc1ncc(CCC(O)=O)c1CC(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Substituted pyrrole
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6694
Blood Brain Barrier+0.53
Caco-2 permeable-0.7613
P-glycoprotein substrateSubstrate0.6005
P-glycoprotein inhibitor INon-inhibitor0.9798
P-glycoprotein inhibitor IINon-inhibitor0.9936
Renal organic cation transporterNon-inhibitor0.8196
CYP450 2C9 substrateNon-substrate0.904
CYP450 2D6 substrateNon-substrate0.7938
CYP450 3A4 substrateNon-substrate0.7691
CYP450 1A2 substrateNon-inhibitor0.8127
CYP450 2C9 inhibitorNon-inhibitor0.956
CYP450 2D6 inhibitorNon-inhibitor0.9395
CYP450 2C19 inhibitorNon-inhibitor0.939
CYP450 3A4 inhibitorNon-inhibitor0.9709
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9959
Ames testNon AMES toxic0.8901
CarcinogenicityNon-carcinogens0.942
BiodegradationNot ready biodegradable0.7077
Rat acute toxicity2.0559 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9522
hERG inhibition (predictor II)Non-inhibitor0.9012
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.72 mg/mLALOGPS
logP-2.4ALOGPS
logP-3.4ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.51 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity54.73 m3·mol-1ChemAxon
Polarizability22.11 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen.
Gene Name:
ALAD
Uniprot ID:
P13716
Molecular Weight:
36294.485 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23